Photosensitizer method to determine rate constants for the reaction of carbonate radical with organic compounds

Environmental Science and Technology

Volumn 39, Issue 23, 2005, Pages 9182-9188

  Canonica, Silvio ^a   Kohn, Tamar ^a,c   Mac, Marek ^b,d   Real, Francisco J ^a,e   Wirz, Jakob ^b   Von Gunten, Urs ^a  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b UNIVERSITY OF BASEL   (Switzerland)

^c Berkeley   (United States)

^d JAGIELLONIAN UNIVERSITY   (Poland)

^e UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HERBICIDES; KETONES; LASERS; ORGANIC COMPOUNDS; OXIDATION; PHOTOLYSIS; PHOTOSENSITIZERS; SOLUTIONS; WATER TREATMENT;

CARBONATE ANION; CARBONATE RADICAL; LASER FLASH PHOTOLYSIS; SUWANNEE RIVER FULVIC ACID;

CARBONATES;

AROMATIC COMPOUND; CARBANILAMIDE DERIVATIVE; CARBONIC ACID; DISSOLVED ORGANIC MATTER; FULVIC ACID; HERBICIDE; KETONE DERIVATIVE; ORGANIC COMPOUND; OXIDIZING AGENT; PHOTOSENSITIZING AGENT; RADICAL; SURFACE WATER; TRIAZINE DERIVATIVE;

CARBONATE; ORGANIC COMPOUND; OXIDATION; PHOTOLYSIS;

AQUATIC ENVIRONMENT; AQUEOUS SOLUTION; ARTICLE; KINETICS; OXIDATION; PHOTOLYSIS; STEADY STATE; TECHNIQUE;

CARBONATES; KINETICS; ORGANIC CHEMICALS;

EID: 28444474518     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es051236b     Document Type: Article

References (49)

1. Weeks, J. L.; Rabani, J. Pulse radiolysis of deaerated aqueous carbonate solutions. 1. Transient optical spectrum and mechanism. 2. pK for OH radicals. J. Phys. Chem. 1966, 70, 2100-2106.
2. Dogliotti, L.; Hayon, E. Flash photolysis of persulfate ions in aqueous solutions. Study of sulfate and ozonide radical anions. J. Phys. Chem. 1967, 71, 2511-2516.
3. Behar, D.; Czapski, G.; Duchovny, I. Carbonate radical in flash photolysis and pulse radiolysis of aqueous carbonate solutions. J. Phys. Chem. 1970, 74, 2206-2210.
4. Chen, S. N.; Hoffman, M. Z.; Parsons, G. H. Reactivity of carbonate radical toward aromatic compounds in aqueous solution. J. Phys. Chem. 1975, 79, 1911-1912.
5. Moore, J. S.; Phillips, G. O.; Sosnowski, A. Reaction of carbonate radical anion with substituted phenols. Int. J. Radiat. Biol. 1977, 31, 603-605.
6. Elango, T. P.; Ramakrishnan, V.; Vancheesan, S.; Kuriacose, J. C. Reaction of the carbonate radical with substituted anilines. Proc. Indian Acad. Sci.-Chem. Sci. 1984, 93, 47-52.
7. -, with anions. J. Phys. Chem. 1990, 94, 8561-8567.
8. Huie, R. E.; Shoute, L. C. T.; Neta, P. Temperature dependence of the rate constants for reactions of the carbonate radical with organic and inorganic reductants. Int. J. Chem. Kinet. 1991, 23, 541-552.
9. Clifton, C. L.; Huie, R. E. Rate constants for some hydrogen abstraction reactions of the carbonate radical. Int. J. Chem. Kinet. 1993, 25, 199-203.
10. Padmaja, S.; Neta, P.; Huie, R. E. Rate constants for some reactions of inorganic radicals with inorganic ions: Temperature and solvent dependence. Int. J. Chem. Kinet. 1993, 25, 447-455.
11. Czapski, G.; Lymar, S.V.; Schwarz, H. A. Acidity of the carbonate radical. J. Phys. Chem. A 1999, 103, 3447-3450.
12. Larson, R. A.; Zepp, R. G. Reactivity of the carbonate radical with aniline derivatives. Environ. Toxicol. Chem. 1988, 7, 265-274.
13. -.) as a reactive intermediate in water chemistry: Kinetics and modelling. Acta Hydrochim. Hydrobiol. 1999, 27, 214-222.
14. Huang, J. P.; Mabury, S. A. A new method for measuring carbonate radical reactivity toward pesticides. Environ. Toxicol. Chem. 2000, 19, 1501-1507.
15. Huang, J. P.; Mabury, S. A. Steady-state concentrations of carbonate radicals in field waters. Environ. Toxicol. Chem. 2000, 19, 2181-2188.
16. Huang, J.; Mabury, S. A. The role of carbonate radical in limiting the persistence of sulfur-containing chemicals in sunlit natural waters. Chemosphere 2000, 41, 1775-1782.
17. Augusto, O.; Bonini, M. G.; Amanso, A. M.; Linares, E.; Santos, C. C. X.; De Menezes, S. L. Nitrogen dioxide and carbonate radical anion: Two emerging radicals in biology. Free Radical Biol. Med. 2002, 32, 841-859.
18. 2-catalyzed one-electron oxidations by peroxynitrite: Properties of the reactive intermediate. Inorg. Chem. 1998, 37, 294-301.
19. 2. Chem. Res. Toxicol. 2001, 14, 1273-1276.
20. 2: Energetics, reactive species, and biological implications. Chem. Res. Toxicol. 2002, 15, 885-895.
21. Buxton, G. V.; Elliot, A. J. Rate constant for reaction of hydroxyl radicals with bicarbonate ions. Radiat. Phys. Chem. 1986, 27, 241-243.
22. Sulzberger, B.; Canonica, S.; Egli, T.; Giger, W.; Klausen, J.; von Gunten, U. Oxidative transformations of contaminants in natural and in technical systems. Chimia 1997, 51, 900-907.
23. Neta, P.; Huie, R. E.; Ross, A. B. Rate constants for reactions of inorganic radicals in aqueous solution. J. Phys. Chem. Ref. Data 1988, 17, 1027-1284.
24. Ferrer-Sueta, G.; Vitturi, D.; Batinic-Haberle, I.; Fridovich, I.; Goldstein, S.; Czapski, G.; Radi, R. Reactions of manganese porphyrins with peroxynitrite and carbonate radical anion. J. Biol. Chem. 2003, 278, 27432-27438.
25. Stenman, D.; Carlsson, M.; Jonsson, M.; Reitberger, T. Reactivity of the carbonate radical anion towards carbohydrate and lignin model compounds. J. Wood Chem. Technol. 2003, 23, 47-69.
26. Kuzmin, V. A.; Chibisov, A. K.; Karyakin, A. V. Decay kinetics of the triplet and anthrasemiquinone radicals in aqueous organic media. Int. J. Chem. Kinet. 1972, 4, 639-644.
27. Scheerer, R.; Grätzel, M. Laser photolysis studies of duroquinone triplet state electron-transfer reactions. J. Am. Chem. Soc. 1977, 99, 865-871.
28. .- radicals generated in the flash photolysis of carbonatoamine complexes of cobalt(III) in aqueous solution. J. Phys. Chem. 1973, 77, 1111-1116.
29. Eriksen, T. E.; Lind, J.; Merenyi, G. On the acid-base equilibrium of the carbonate radical. Radiat. Phys. Chem. 1985, 26, 197-199.
30. Scheerer, R.; Grätzel, M. Photoinduced oxidation of carbonate ions by duroquinone, a pathway of oxygen evolution from water by visible light. Ber. Bunsen-Ges. Phys. Chem. 1976, 80, 979-982.
31. Canonica, S.; Jans, U.; Stemmler, K.; Hoigné, J. Transformation kinetics of phenols in water: Photosensitization by dissolved natural organic material and aromatic ketones. Environ. Sci. Technol. 1995, 29, 1822-1831.
32. Canonica, S.; Hellrung, B.; Wirz, J. Oxidation of phenols by triplet aromatic ketones in aqueous solution. J. Phys. Chem. A 2000, 104, 1226-1232.
33. Gerecke, A. C.; Canonica, S.; Muller, S. R.; Scharer, M.: Schwarzenbach, R. P. Quantification of dissolved natural organic matter (DOM) mediated phototransformation of phenylurea herbicides in lakes. Environ. Sci. Technol. 2001, 35, 3915-3923.
34. Wegelin, M.; Canonica, S.; Mechsner, K.; Fleischmann, T.; Pesaro, F.; Metzler, A. Solar water disinfection: Scope of the process and analysis of radiation experiments. J. Water Supply Res. Technol. - AQUA 1994, 43, 154-169.
35. Hasler, E.; Hörmann, A.; Persy, G.; Platsch, H.; Wirz, J. Singlet and triplet biradical intermediates in the valence isomerization of 2,7-dihydro-2,2,7,7-tetramethylpyrene. J. Am. Chem. Soc. 1993, 115, 5400-5409.
36. Canonica, S.; Freiburghaus, M. Electron-rich phenols for probing the photochemical reactivity of freshwaters. Environ. Sci. Technol. 2001, 35, 690-695.
37. Hurley, J. K.; Linschitz, H.; Treinin, A. Interaction of halide and pseudohalide ions with triplet benzophenone-4-carboxylate - Kinetics and radical yields. J. Phys. Chem. 1988, 92, 5151-5159.
38. Loeff, I.; Rabani, J.; Treinin, A.; Linschitz, H. Charge-transfer and reactivity of nπ* and ππ* organic triplets, including anthraquinonesulfonates, in interactions with inorganic anions: A comparative study based on classical Marcus theory. J. Am. Chem. Soc. 1993, 115, 8933-8942.
39. Mac, M.; Wirz, J.; Najbar, J. Transient radicals formed by electron transfer between inorganic ions and excited aromatic molecules in polar solvents. Helv. Chim. Acta 1993, 76, 1319-1331.
40. Huie, R. E.; Clifton, C. L.; Neta, P. Electron-transfer reaction rates and equilibria of the carbonate and sulfate radical anions. Radiat. Phys. Chem. 1991, 38, 477-481.
41. Treinin, A.; Loeff, I.; Hurley, J. K.; Linschitz, H. Charge-transfer interactions of excited molecules with inorganic anions: The role of spin-orbit coupling in controlling net electron-transfer. Chem. Phys. Lett. 1983, 95, 333-338.
42. Stanbury, D. M. Reduction potentials involving inorganic free radicals in aqueous solution. Adv. Inorg. Chem. 1989, 33, 69-138.
43. Canonica, S.; Tratnyek, P. G. Quantitative structure-activity relationships for oxidation reactions of organic chemicals in water. Environ. Toxicol. Chem. 2003, 22, 1743-1754.
44. Jonsson, M.; Lind, J.; Eriksen, T. E.; Merenyi, G. O-H Bond strengths and one-electron reduction potentials of multisubstituted phenols and phenoxyl radicals. Predictions using free-energy relationships. J. Chem. Soc.-Perkin Trans. 2 1993, 1567-1568.
45. Brezonik, P. L.; Fulkerson-Brekken, J. Nitrate-induced photolysis in natural waters: Controls on concentrations of hydroxyl radical photointermediates by natural scavenging agents. Environ. Sci. Technol. 1998, 32, 3004-3010.
46. Hoigné, J. Formulation and calibration of environmental reaction kinetics: Oxidations by aqueous photooxidants as an example. In Aquatic Chemical Kinetics: Reaction Rates of Processes in Natural Waters; Stumm, W., Ed.; Wiley-Interscience: New York, 1990; pp 43-70.
47. Tixier, C.; Singer, H. P.; Canonica, S.; Muller, S. R. Phototransformation of triclosan in surface waters: A relevant elimination process for this widely used biocide - Laboratory studies, field measurements, and modeling. Environ. Sci. Technol. 2002, 36, 3482-3489.
48. Mopper, K.; Zhou, X. L. Hydroxyl radical photoproduction in the sea and its potential impact on marine processes. Science 1990, 250, 661-664.
49. von Gunten, U. Ozonation of drinking water: Part I. Oxidation kinetics and product formation. Water Res. 2003, 37, 1443-1467.